Literature DB >> 12109110

Synthesis of amino acid derivatives via enantio- and diastereoselective Pd-catalyzed allylic substitutions with a non-stabilized enolate as nucleophile.

Thomas D Weiss1, Günter Helmchen, Uli Kazmaier.   

Abstract

Diastereomer ratios of up to 95:5 and enantiomeric excesses of up to 95% were achieved in Pd-catalyzed asymmetric alyllic substitutions with zinc enolates of glycine esters as nucleophiles; a remarkable effect of the ligand on the diastereoselectivity of the substitution was found.

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Year:  2002        PMID: 12109110     DOI: 10.1039/b203791m

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  4 in total

1.  Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates.

Authors:  Xingyu Jiang; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-27       Impact factor: 15.336

2.  Palladium-catalyzed allylic alkylation of carboxylic acid derivatives: N-acyloxazolinones as ester enolate equivalents.

Authors:  Barry M Trost; David J Michaelis; Julie Charpentier; Jiayi Xu
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-16       Impact factor: 15.336

3.  PREPARATION OF (S)-tert-ButylPHOX (Oxazole, 4-(1,1-dimethylethyl)-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro- (4S)-).

Authors:  Michael R Krout; Justin T Mohr; Brian M Stoltz
Journal:  Organic Synth       Date:  2009-01-01

4.  Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism.

Authors:  Da-Chang Bai; Fei-Le Yu; Wan-Ying Wang; Di Chen; Hao Li; Qing-Rong Liu; Chang-Hua Ding; Bo Chen; Xue-Long Hou
Journal:  Nat Commun       Date:  2016-06-10       Impact factor: 14.919

  4 in total

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